p-Toluenesulfonic acid → 2-(2,6-Dimethylpyridin-4-yl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 591803ノート

反応式

HRID 591803 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:13]=1[C:14]([NH2:16])=[O:15].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:16][C:14](=[O:15])[C:13]3[C:12](=[CH:20][C:19]([O:21][CH3:22])=[CH:18][C:17]=3[O:23][CH3:24])[N:11]=2)[CH:5]=[C:4]([CH3:10])[N:3]=1

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 27630042,6-Dimethylpyridine-4-carbaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

生成物 1

HCID 1359390642-(2,6-Dimethylpyridin-4-yl)-5,7-dimethoxyquinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 2,6-dimethylpyridine-4-carbaldehyde (0.14 g, 1.00 mmol) in N,N-dimethyl acetamide (10 mL) were added 2-amino-4,6-dimethoxybenzamide (0.20 g, 1.00 mmol), sodium hydrogen sulfite (0.21 g, 2.00 mmol), and p-toluenesulfonic acid (0.28 g, 1.50 mmol). The reaction mixture was stirred at 110° C. for 16 hours under nitrogen. After cooling to room temperature, solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution (30 mL), water (30 mL), and brine (30 mL), and dried over anhydrous sodium sulfate. Solvent was evaporated, and the residue was purified by column chromatography (silica gel 230-400 mesh; 2-5% methanol in dichloromethane as eluent) to give the title compound as a yellow solid. Yield: 0.030 g (10%). MP 291-292° C. 1H NMR (400 MHz, CDCl3): δ 9.86 (br s, 1H), 7.60 (s, 2H), 6.87 (d, J=2.2 Hz, 1H), 6.53 (d, J=2.2 Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H), 2.66 (s, 6H). MS (ES) m/z: 312.50 (M+1) (100%).

後処理

  1. temperatureAfter cooling to room temperature
  2. customsolvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 solution (30 mL), water (30 mL), and brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSolvent was evaporated
  7. customthe residue was purified by column chromatography (silica gel 230-400 mesh; 2-5% methanol in dichloromethane as eluent)

出典と根拠

ORDレコード
ord-cb18bf13d7e64872b735b10d274aeb13
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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